Process for producing fat composition containing hydrophobic components of glycyrrhiza

ABSTRACT

In the present invention, an oil and fat composition containing 10% by weight or more of a specific fat-soluble polyhydric fatty acid ester, in particular, a glycerol fatty acid ester, is used as a solvent for extracting hydrophobic components from licorice. Consequently, it is possible to reduce the production costs for hydrophobic components of licorice which have excellent effects as food and drink, such as health food and food with health claims (food for specified health uses and food with nutrient function claims), pharmaceutical products, etc. It is also possible to improve the stability and handling properties of the resulting composition.

RELATED APPLICATIONS

This application is a nationalization of PCT application No.PCT/JP03/04312 filed on Apr. 4, 2003, claiming priority to JapaneseApplication No. 2002-102629 filed on Apr. 4, 2002.

TECHNICAL FIELD

The present invention relates to a process for producing an oil and fatcomposition containing hydrophobic components of glycyrrhiza (licorice)and being suitable for use in preparing food and drink, such as healthfood and food with health claims (food for specified health uses andfood with nutrient function claims), pharmaceutical products, etc.

BACKGROUND ART

Licorice and a water extract thereof have been used as galenicals havinganalgesic and antispasmodic actions and an expectorant action, or infood applications. Since glycyrrhizin (glycyrrhizinic acid), which is amain component of licorice, is about 200 times sweeter than sucrose, itis also used as a sweetening agent.

It has also been confirmed that hydrophobic components extracted fromlicorice or a water-extracted residue of licorice with an organicsolvent, such as ethanol, acetone, or ethyl acetate, have many usefuleffects, such as an antioxidant effect, an antibacterial effect, anenzyme inhibitory effect, an antitumor effect, an antiallergic effect,and an antiviral effect. Furthermore, recent research has found that thehydrophobic components of licorice have a hypoglycemic action and alipid metabolism-improving action (WO02/47699).

In order to extract such hydrophobic components from licorice, organicsolvents are exclusively used. For example, each of Japanese UnexaminedPatent Application Publications Nos. 1-149706 and 3-109314 discloses anexample of extraction with a hydrophobic organic solvent; JapaneseUnexamined Patent Application Publication No. 2-204495 discloses anexample of extraction with a mixed solvent of a hydrophobic organicsolvent and a small amount of water-soluble organic solvent; JapaneseUnexamined Patent Application Publication No. 7-53393 discloses anexample of extraction with water and/or a water-soluble organic solvent(preferably, hot water); and Japanese Unexamined Patent ApplicationPublication No. 1-157909 discloses an example of extraction with one ofa wide variety of water-soluble organic solvents and hydrophobic organicsolvents.

However, the resulting hydrophobic components of licorice do notsubstantially dissolve in water and common oil, and the extract obtainedwith such an organic solvent easily cakes and colors, thus beingunstable. Therefore, the extract must be formulated so as to be easy tohandle and stable. In any of the methods described above, the organicsolvent used for extraction results in many unsolved problems, forexample, a high production cost and a significant adverse effect on theenvironment.

SUMMARY OF THE INVENTION

As described above, hydrophobic components of licorice are highlyeffective in preparing food and drink, such as health food and food withhealth claims (food for specified health uses and food with nutrientfunction claims), pharmaceutical products, etc. However, the productioncost therefor is high because of the extraction process using an organicsolvent only, and the extract is difficult to handle, resulting indifficulty in utilization. Accordingly, it is an object of the presentinvention to inexpensively obtain hydrophobic components of licoricewhich are suitable for use in preparing food and which are stable andeasy to handle.

The present inventors have conducted intensive research and have foundthat the object described above can be achieved by using a specificfat-soluble polyhydric alcohol fatty acid ester as a solvent and havealso found that an oil and fat composition which can be used in allapplications of usual edible oils and fats can be produced. The presentinvention has been completed based upon these findings.

That is, in a first aspect, the present invention relates to a processfor producing an oil and fat composition containing hydrophobiccomponents of licorice, including mixing licorice with an oil and fatsolvent containing 10% by weight or more of a fat-soluble polyhydricalcohol fatty acid ester.

Preferably, the process for producing the oil and fat compositioncontaining hydrophobic components of licorice according to the presentinvention further includes using at least one organic solvent selectedfrom the group consisting of ethanol, acetone, and ethyl acetate.Preferably, the process for producing the oil and fat compositioncontaining hydrophobic components of licorice includes the steps ofmixing at least one organic solvent selected from the group consistingof ethanol, acetone, and ethyl acetate with licorice, and then mixingthe oil and fat solvent containing 10% by weight or more of thefat-soluble polyhydric alcohol fatty acid ester therewith. In theprocess for producing the oil and fat composition containing hydrophobiccomponents of licorice, preferably, the oil and fat solvent is composedof only the fat-soluble polyhydric alcohol fatty acid ester. In theprocess for producing the oil and fat composition containing hydrophobiccomponents of licorice, preferably, the fat-soluble polyhydric alcoholfatty acid ester is a glycerol fatty acid ester. In the process forproducing the oil and fat composition containing hydrophobic componentsof licorice, preferably, the glycerol fatty acid ester is amonoglyceride and/or a diglyceride. In the process for producing the oiland fat composition containing hydrophobic components of licorice,preferably, the glycerol fatty acid ester is a medium-chaintriglyceride. In the process for producing the oil and fat compositioncontaining hydrophobic components of licorice, preferably, the glycerolfatty acid ester is a polyglycerol fatty acid ester. In the process forproducing the oil and fat composition containing hydrophobic componentsof licorice, preferably, the polyglycerol fatty acid ester is apolyglycerol condensed ricinoleic acid ester.

In a second aspect, the present invention relates to an oil and fatcomposition containing hydrophobic components of licorice obtained byany one of the production processes described above.

In a third aspect, the present invention relates to an oil andfat-containing food including the oil and fat composition containing thehydrophobic components of licorice described above.

DETAILED DISCLOSURE OF THE INVENTION

The present invention will be described in detail below.

According to the present invention, a process for producing an oil andfat composition containing hydrophobic components of licorice includesmixing an oil and fat solvent containing 10% by weight or more of afat-soluble polyhydric alcohol fatty acid ester with licorice.

First, examples of licorice which may be used in the present inventioninclude leguminous plants of the genus Glycyrrhiza, such as Glycyrrhizauralensis (G. uralensis), Glycyrrhiza inflata (G. inflata), Glycyrrhizaglabra (G. glabra), Glycyrrhiza eurycarpa (G. eurycarpa), andGlycyrrhiza aspera (G. aspera). Preferred examples include G. uralensis,G. inflata, and G. glabra. Licorice has long been eaten as food and hasalso been used as a food additive or a galenical.

Examples of the form of licorice used in the present invention includelicorice itself, licorice powder, a water-extracted residue obtained byremoving hydrophilic components by extraction with water or the likefrom licorice or licorice powder, and a dried product of thewater-extracted residue. However, an extract obtained by a method inwhich licorice is subjected to extraction with a common organic solvent(e.g., ethanol, acetone, or ethyl acetate) and the organic solvent isthen removed is not considered as the form of licorice used in thepresent invention.

Next, the solvent used in the present invention is an oil and fatsolvent containing 10% by weight or more of a fat-soluble polyhydricalcohol fatty acid ester. If the content of the fat-soluble polyhydricalcohol fatty acid ester is 10% by weight or more, the effect ofextracting hydrophobic components from licorice is satisfactorilyexhibited.

Any fat-soluble polyhydric alcohol fatty acid ester having at least twohydroxyl groups per molecule can be used in the present invention.Examples thereof include fatty acid esters of glycerol, polyglycerol,sugars, sugar alcohols, and polysorbates. Above all, in view of the higheffect of extracting hydrophobic components from licorice, preferred arefat-soluble polyhydric alcohol fatty acid esters having a HLB of 7.0 orless and polyglycerol condensed ricinoleic acid esters which arefat-soluble even with a HLB of more than 7.0. These may be used alone orin combination.

Additionally, the HLB can be determined by the following expression(Kagaku Jiten, first edition, Tokyo Kagaku Dozin Co., Ltd., published onOct. 1, 1994):HLB=20×(1−S/A),where S is the saponification number of the ester and A is the acidnumber of the fatty acid.

As the glycerol fatty acid ester, any ester of glycerol or polyglyceroland the fatty acid which will be described below can be used withoutlimitation. Preferred are glycerol fatty acid esters having a HLB of 7.0or less and polyglycerol condensed ricinoleic acid esters which arefat-soluble even with a HLB of more than 7.0. In view of the high effectof extracting hydrophobic components from licorice, preferred aremonoglycerides and diglycerides. In the case of triglycerides,medium-chain triglycerides are preferable. Polyglycerol fatty acidesters are also preferable. As the polyglycerol fatty acid ester, apolyglycerol condensed ricinoleic acid ester is more preferable.Furthermore, compound lipids, such as phospholipids, may be used.Monoglycerides, diglycerides, and compound lipids, such asphospholipids, are contained as accessory constituents in natural oilsand fats and widely used in the food field.

Examples of fatty acid residues constituting the esters described aboveinclude those having 4 to 24 carbon atoms. Among them, examples ofmedium-chain fatty acid residues include those having 8 to 10 carbonatoms. Saturated fatty acids and unsaturated fatty acids thereof may beselected depending on application. For example, when flowability isrequired, unsaturated fatty acids are preferred. When plasticity isrequired, saturated fatty acids may be contained. Branched-chain fattyacids, such as isostearic acid, may also be used.

Examples of the saturated fatty acids include caproic acid, caprylicacid, capric acid, lauric acid, myristic acid, palmitic acid, stearicacid, and behenic acid. Examples of the unsaturated fatty acids includeoleic acid, linoleic acid, linolenic acid, and ricinoleic acid.Furthermore, ricinoleic acid may form a condensed acid.

In addition to the fat-soluble polyhydric alcohol fatty acid ester,animal and vegetable oils and fats may also be incorporated into the oiland fat solvent used in the present invention. Examples of the animaland vegetable oils and fats include vegetable oils, such as corn oil,rapeseed oil, rapeseed oil with a high erucic acid content, soybean oil,olive oil, safflower oil, cottonseed oil, sunflower oil, rice bran oil,palm oil, and palm kernel oil; animal oils, such as fish oil, beeftallow, lard, milk fat, and yolk oil; oils and fats produced byfractionation, hydrogenation, transesterification, or the like usingthese oils as starting materials; and mixtures of these oils and fats.

The content of the fat-soluble polyhydric alcohol fatty acid ester inthe oil and fat solvent must be 10% by weight or more, as describedabove. The content of the fat-soluble polyhydric alcohol fatty acidester in the oil and fat solvent is preferably 20% by weight or more,more preferably 30% by weight or more, still more preferably 50% byweight or more, and particularly preferably 100% by weight.

In the process for producing the oil and fat composition containinghydrophobic components of licorice according to the present invention,the oil and fat solvent is mixed with licorice. Specifically, forexample, after the licorice in the above described form and the oil andfat solvent containing the fat-soluble polyhydric alcohol fatty acidester are stirred, insolubles may be removed by centrifugation,filtration under reduced pressure, pressure filtration, filter pressing,or the like.

In order to improve extraction efficiency, stirring is preferablyperformed under heating preferably at 30° C. to 100° C., and morepreferably at 40° C. to 90° C. In order to prevent degradation due toheating, more preferably stirring is performed under reduced pressure orunder nitrogen flow. The stirring time is preferably 1 hour or more,more preferably 1 to 5 hours, and most preferably 1 to 3 hours, althoughnot particularly limited thereto.

Furthermore, from the standpoint of improving the extraction efficiency,the oil and fat solvent is preferably used together with an organicsolvent, such as ethanol, acetone, or ethyl acetate, which is commonlyused for extraction of hydrophobic components of licorice, andparticularly preferably ethanol. In such a case, the amount of theorganic solvent used can be decreased compared with the conventionalprocess. Furthermore, an edible oil and fat composition containinghydrophobic components of licorice can also be obtained merely byremoving the organic solvent by distillation. Thereby, it is possible toreduce costs by simplifying the production process.

Specifically, licorice may be mixed with a mixed solvent including theoil and fat solvent containing 10% by weight or more of the fat-solublepolyhydric alcohol fatty acid ester and at least one organic solventselected from the group consisting of ethanol, acetone, and ethylacetate. Alternatively, at least one organic solvent selected from thegroup consisting of ethanol, acetone, and ethyl acetate may be mixedwith licorice, and then the oil and fat solvent containing 10% by weightor more of the fat-soluble polyhydric alcohol fatty acid ester may bemixed therewith.

In either case, by removing the organic solvent after the stirring step,an oil and fat composition containing hydrophobic components of licoricecan be obtained. Additionally, when the oil and fat solvent is mixedafter the organic solvent is mixed with licorice, the organic solvent isremoved by distillation after mixing the oil and fat solvent andsubsequent stirring, not before mixing the oil and fat solvent. If theorganic solvent is removed by distillation before the oil and fatsolvent is mixed, it becomes difficult to dissolve the residue in theoil and fat solvent, and as a result, a large amount of solvent must beused, the stirring temperature must be increased, or the stirring timemust be extended.

In the production method of the present invention, the amounts oflicorice, the oil and fat solvent, and the organic solvent used are notparticularly limited. When the oil and fat solvent alone is used as thesolvent, the amount of the oil and fat solvent is preferably 50 parts byweight or more and more preferably 100 to 500 parts by weight to 100parts by weight of licorice.

When both the oil and fat solvent and the organic solvent are used, theamount of the oil and fat solvent is preferably 10 parts by weight ormore and more preferably 10 to 250 parts by weight, and the amount ofthe organic solvent is preferably 50 to 500 parts by weight and morepreferably 50 to 250 parts by weight, to 100 parts by weight oflicorice. In such a case, the ratio of the oil and fat solvent to theorganic solvent (oil and fat solvent/organic solvent) is preferably 0.01to 10 and more preferably 0.1 to 5.

The resultant oil and fat composition containing hydrophobic componentsof licorice can be used as the oil and fat composition of the presentinvention in the form of a crude extract or semipurified extract as longas it does not contain impurities inappropriate for use aspharmaceutical products or food. The resultant oil and fat compositionmay be subjected to purification treatment, such as decolorization anddeodorization, using various adsorbents, etc., if necessary.

The oil and fat composition containing hydrophobic components oflicorice according to the present invention contains flavonoidcomponents, which have medicinal properties, for example, glycycoumarin,glycyrol, glycyrin, liquiritigenin, glicoricone, glabridin, glabrene,glabrol, 3′-hydroxyl-4′-O-methylglabridin, 4′-O-methylglabridin,hyspaglabridin B, glyurallin B, licocoumarone, gancaonin I,dehydroglyasperin D, echinatin, isolicoflavonol, dehydroglyasperin C,glyasperin B, glycyrrhisoflavanone, lupiwighteone, glyasperin D, andsemilicoisoflavone B. The higher contents of these components arepreferable in view of the hypoglycemic action and the lipidmetabolism-improving action.

The oil and fat composition of the present invention may be used alonefor food to be cooked or in preparing soft capsules, etc. In addition,since the oil and fat composition of the present invention is misciblewith a fat object, the physical properties of the composition may beadjusted by adding another edible oil and fat depending on the purpose.In such a case, the type and the amount of the other edible oil and fatused are determined in consideration of various conditions, such as thephysical properties required for the product and the service temperaturerange. By adjusting the type and the amount of the other edible oil andfat to be added, properties, such as consistency and melting point, canbe controlled.

As the other edible oils and fats, the same animal and vegetable oilsand fats as those usable in combination with the fat-soluble polyhydricalcohol fatty acid ester as the oil and fat solvent, which have beendescribed above, may be used. Examples thereof include vegetable oils,such as corn oil, rapeseed oil, rapeseed oil with a high erucic acidcontent, soybean oil, olive oil, safflower oil, cottonseed oil,sunflower oil, rice bran oil, palm oil, and palm kernel oil; animaloils, such as fish oil, beef tallow, lard, milk fat, and yolk oil; oilsand fats produced by fractionation, hydrogenation, transesterification,or the like using these oils as starting materials; and mixtures ofthese oils and fats.

The edible oil and fat compositions thus obtained can be used as liquidoils and fats, such as frying oils; and as oils and fats havingplasticity, such as margarine and shortening. The edible oil and fatcompositions can also be used for water-in-oil emulsions andoil-in-water emulsions.

Examples of the oil and fat-containing food containing the oil and fatcomposition of the present invention include confectionery, such aschewing gum, chocolates, candies, jelly, mousses, biscuits, andcrackers; frozen desserts, such as ice cream and sherbet; beverages,such as tea, soft drinks, nutrition supplement drinks, and beautydrinks; noodles and pasta, such as Japanese wheat noodles, Chinesenoodles, spaghetti, and instant noodles; fish paste products, such askamaboko (fish cake), chikuwa (tubular fish cake), and hanpen (softwhite fish cake); flavoring materials, such as dressings, mayonnaise,and sauce; and other foods, such as bread, ham, soup, various types ofretort pouch food, and various types of frozen food. The oil andfat-containing food can also be used for pet food, feedstuff, etc.

Furthermore, for the purpose of enrichment, various vitamins such as A,D, and E may be incorporated into or used in combination with the oiland fat-containing food. As taste enhancers, various flavors and dairysubstances, such as whole milk powder, skim milk powder, fermented milk,all kinds of salts, and milk fat, may also be incorporated into or usedin combination with the oil and fat-containing food.

Besides the additives described above, it is possible to use all theadditives, such as antioxidants and coloring agents, that are used forusual water-in-oil emulsions and oil-in-water emulsions.

The oil and fat-containing food can be produced incorporating the oiland fat composition of the present invention using a conventional methoddepending on the type, the form, and the like.

BEST MODE FOR CARRYING OUT THE INVENTION

While the present invention will be described in detail based on theexamples below, it is to be understood that the invention is not limitedthereto. In the following description, the terms “parts” and “%” mean“parts by weight” and “% by weight”, respectively.

EXAMPLE 1

Licorice powder (kaneka San Spice Co., Ltd.) in an amount of 30 partswas mixed with 100 parts of a glycerol fatty acid ester (Sunfat GDO-D,Taiyo Kagaku Co., Ltd.; HLB=3.0; fatty acid moiety: mainly composed ofoleic acid; monoglycerides 4% and diglycerides 96%), and the mixture wasstirred under reduced pressure at 60° C. for 3 hours. Insolubles werethen removed by filtration under reduced pressure. Oil and fatComposition 1 was thereby obtained.

EXAMPLE 2

Oil and fat Composition 2 was obtained with the same mixing ratio andoperation as those in Example 1 except that a glycerol fatty acid ester(Poem Z-500, Riken Vitamin Co., Ltd.; HLB=3.1; fatty acid moiety: mainlycomposed of oleic acid and linoleic acid; monoglycerides 40%,diglycerides 45%, and triglycerides 15%) was used.

EXAMPLE 3

Oil and fat Composition 3 was obtained with the same mixing ratio andoperation as those in Example 1 except that a medium-chain triglyceride(Actor M2, Riken Vitamin Co., Ltd.; HLB=0; fatty acid moiety: mainlycomposed of caprylic acid) was used.

EXAMPLE 4

Licorice powder (Kaneka San Spice Co., Ltd.) in an amount of 30 partswas mixed with 50 parts of a medium-chain triglyceride (Actor M2, RikenVitamin Co., Ltd.; HLB=0; fatty acid moiety: mainly composed of caprylicacid) and 50 parts of 95% ethanol, and the mixture was stirred at 40° C.for 1 hour. Insolubles were then removed by filtration under reducedpressure, and ethanol was removed by distillation. Oil and fatComposition 4 was thereby obtained.

EXAMPLE 5

Licorice powder (Kaneka San Spice Co., Ltd.) in an amount of 30 partswas mixed with 150 parts of 95% ethanol, and the mixture was stirred atroom temperature for 3 hours. After insolubles were removed byfiltration under reduced pressure, 20 parts of a medium-chaintriglyceride (Actor M2, Riken Vitamin Co., Ltd.; HLB=0; fatty acidmoiety: mainly composed of caprylic acid) was mixed therewith. Stirringwas performed at 40° C. for 1 hour, and then ethanol was removed bydistillation. Oil and fat Composition 5 was thereby obtained.

EXAMPLE 6

Licorice powder (Kaneka San Spice Co., Ltd.) in an amount of 30 partswas mixed with 150 parts of 95% ethanol, and the mixture was stirred atroom temperature for 3 hours. Insolubles were then removed by filtrationunder reduced pressure. A mixture of 18 parts of rapeseed oil (KanekaCorporation) and 2 parts of a polyglycerol condensed ricinoleic acidester (SY Glyster CRS-75, Sakamoto Yakuhin Kogyo Co., Ltd.; fatty acidmoiety: ricinoleic acid) was added thereto, and the mixture was stirredat 40° C. for 1 hour. Ethanol was then removed by distillation. Oil andfat Composition 6 was thereby obtained.

COMPARATIVE EXAMPLE 1

Licorice powder (Kaneka San Spice Co., Ltd.) in an amount of 30 partswas mixed with 150 parts of 95% ethanol, and the mixture was stirred atroom temperature for 3 hours. Insolubles were removed by filtrationunder reduced pressure, and ethanol was removed by distillation to yield1.5 parts of a licorice extract. A glycerol fatty acid ester (SunfatGDO-D, Taiyo Kagaku Co., Ltd.; HLB=3.0; fatty acid moiety: mainlycomposed of oleic acid) in an amount of 100 parts was added to thelicorice extract, and the extract was dissolved by stirring at 40° C.for 1 hour. Oil and fat Composition 7 containing hydrophobic componentsof licorice was thereby obtained.

This process requires large amounts of the organic solvent and the oiland fat solvent in order to extract the hydrophobic components fromlicorice and to dissolve the extract. Consequently, the oil and fatcomposition containing the hydrophobic components of licorice was notproduced inexpensively and did not have excellent handling properties.

COMPARATIVE EXAMPLE 2

A medium-chain triglyceride (Actor M2, Riken Vitamin Co., Ltd.; HLB=0;fatty acid moiety: mainly composed of caprylic acid) in an amount of 20parts was mixed with 1.5 parts of a licorice extract obtained as inComparative Example 1. Although the licorice extract was attempted to bedissolved in the medium-chain triglyceride by stirring at 40° C. for 10hours, the extract was not completely dissolved. As a result, filtrationwas performed under reduced pressure to obtain Oil and fat Composition 8containing hydrophobic components of licorice. The amount of theundissolved licorice extract was about 30% by weight.

In this process, the same amount of the oil and fat solvent was used andstirring was performed at the same temperature as that in Example 5.Even with a longer stirring time, the licorice extract could not becompletely dissolved. Consequently, the oil and fat compositioncontaining the hydrophobic components of licorice was not producedinexpensively and did not have excellent handling properties.

EXPERIMENTAL EXAMPLE 1

<Polyphenol Analysis>

With respect to Oil and fat Compositions 1 to 8 obtained in Examples 1to 6 and Comparative Examples 1 and 2 and the licorice extract obtainedin Comparative Example 1, the polyphenol content (flavonoid content) wasdetermined by the Folin-Denis method using (+)-catechin as standard. Theanalytical results are shown in Table 1 below.

Herein, the observed value of the polyphenol content is determined bythe method described above. The theoretical value of the polyphenolcontent is calculated, on the basis of the polyphenol content in thelicorice extract obtained in Comparative Example 1, according to thefollowing equation:

$\begin{matrix}{\begin{matrix}{{Polyphenol}\;} \\{{content}\mspace{14mu}(\%)}\end{matrix} = \frac{{{Licorice}\mspace{14mu}{{extract}{\mspace{11mu}\;}(g)}\; \times {Polyphenol}\mspace{14mu}{content}\mspace{14mu}{in}\mspace{14mu}{licorice}\mspace{14mu}{extract}\mspace{14mu}(\%)}}{{{Licorice}\mspace{14mu}{{extract}{\mspace{11mu}\;}(g)}} + {{Oil}\mspace{14mu}{and}\mspace{14mu}{fat}\mspace{14mu}{solvent}\mspace{14mu}(g)}}} \\{= \frac{1.5\mspace{14mu}(g) \times 28.012\mspace{14mu}(\%)}{{1.5\mspace{14mu}(g)} + {{Oil}\mspace{14mu}{and}\mspace{14mu}{fat}\mspace{14mu}{solvent}\mspace{11mu}(g)}}}\end{matrix}\mspace{14mu}$

As is evident from Table 1, when the polyphenol content in the licoriceextract obtained in Comparative Example 1 is taken as the reference, thepolyphenol content in each of Oil and fat Compositions 1 to 6 of thepresent invention exceeds 96%. It is thus confirmed that the oil and fatcompositions obtained by the production processes of the presentinvention are highly useful.

TABLE 1 Observed Licorice/Oil Theoretical polyphenol and fat polyphenolExtraction content (weight content rate (wt. %) ratio) (wt. %) (%) Oiland fat 0.399 0.3 0.414 96.4 composition 1 according to Example 1 Oiland fat 0.403 0.3 0.414 97.3 composition 2 according to Example 2 Oiland fat 0.405 0.3 0.414 97.8 composition 3 according to Example 3 Oiland fat 0.803 0.6 0.816 98.4 composition 4 according to Example 4 Oiland fat 1.945 1.5 1.954 99.5 composition 5 according to Example 5 Oiland fat 1.897 1.5 1.954 97.1 composition 6 according to Example 6 Oiland fat 0.414 0.3 0.414 100.0 composition 7 according to ComparativeExample 1 Oil and fat 1.331 1.5 1.954 68.1 composition 8 according toComparative Example 2 Licorice extract 28.012 — — — according toComparative Example 1

EXPERIMENTAL EXAMPLE 2

<Preparation of Samples for HPLC Analysis>

Acetone (90 μl) was added to 10 μl of each of Oil and fat Compositions 1to 6 obtained in Examples 1 to 6 to prepare a solution. The resultingsolutions were diluted 10 times with methanol for HPLC to preparesamples for analysis. A methanol solution (1 mg/ml) of the licoriceextract obtained in Comparative Example 1 was prepared as a sample foranalysis.

<HPLC Conditions>

Column: Nacalai Tesque, COSMOSIL 5C18ARII, 4.6×250 mm

Column temperature: 40° C.

Mobile phase: A=water:acetic acid (55:5=v/v)

-   -   B=acetonitrile

Gradient: The percentage of B to the mobile phase A was maintained at20% for 10 minutes from the start of analysis, increased at a constantrate so that the percentage reached 70% after 60 minutes, and maintainedat 70% from 60 minutes to 70 minutes.

Flow rate: 1 ml/minute

Wavelength: 254 nm

Injected sample amount: 20 μl

<Analytical Results>

As a result of comparison of the individual HPLC analytical charts, itis found that the peaks in each of Oil and fat Compositions 1 to 6 ofthe present invention are exactly identical to the peaks of thehydrophobic components of licorice obtained by ethanol extraction inComparative Example 1. The concentrations of the hydrophobic componentsof licorice estimated based on the peak area are close to thetheoretical values. It is thus confirmed that the oil and fatcompositions obtained by the production processes of the presentinvention are highly useful.

Example 7

<Preparation of Oil Phase>

Oil and fat Composition 1 (15 parts) obtained in Example 1 and rapeseedoil (15 parts) were mixed with each other under heating at 70° C., andlecithin (0.1 parts) and a polyglycerol fatty acid ester (0.1 parts)were dissolved therein in that order to prepare an oil phase.

<Preparation of Aqueous Phase>

An albuminous protein (1 part) and skim milk (60 parts) were heated to50° C., and a sucrose fatty acid ester (0.1 parts) and granulated sugar(10 parts) were added thereto to prepare an aqueous phase.

<Preparation of Oil-in-Water Emulsion>

The aqueous phase and the oil phase prepared as described above werepreliminarily emulsified and then sterilized at 145° C. for 4 secondswith a UHT sterilizer. Subsequently, after vacuum cooling, the mixturewas homogenized at a pressure of 90 kg/cm² with a homogenizer and thenplate-cooled to 10° C. to prepare a cream.

<Preparation of Mousse>

Granulated sugar (13 parts), isomerized sugar (10 parts), and a gellingagent (1 part) were dissolved in water (51 parts) under heating at 90°C., and cream (15 parts) and yogurt (10 parts) were mixed therewith. ThepH was adjusted to 4.0 with citric acid. The resulting mixture wascharged into a cup, sterilized at 85° C. for 20 minutes, and cooled toobtain a mousse.

EXAMPLE 8

<Preparation of Oil Phase>

Oil and fat Composition 3 (70 parts) obtained in Example 3, hardenedcorn oil (melting point 40° C., 30 parts), and lecithin (0.5 parts) weremixed with each other under heating at 60° C. to prepare an oil phase.

<Production of Margarine>

Water (16.5%) was added to the resulting oil phase (83.5%) whilestirring to perform emulsification for 20 minutes. The mixture waskneaded under cooling with a combinator to produce margarine.

EXAMPLE 9

Using a mixture of soft flour (100 parts), the margarine produced inExample 8 (35 parts), white superior soft sugar (40 parts), whole egg (5parts), salt (0.5 parts), and water (18 parts), biscuits were producedaccording to a conventional method.

INDUSTRIAL APPLICABILITY

In accordance with the present invention, it is possible to produce anoil and fat composition containing hydrophobic components of licoriceinexpensively and with excellent stability and handling properties.Furthermore, food and drink, such as health food and food with healthclaims (food for specified health uses and food with nutrient functionclaims), pharmaceutical products, pet food, feedstuff, etc. whichinclude the oil and fat composition of the present invention have ahypoglycemic action and a lipid metabolism-improving action, and thusare significantly advantageous in industrial applications.

1. A process for producing an oil and fat composition containinghydrophobic components of licorice, comprising mixing licorice with anoil and fat solvent containing 10% by weight or more of a fat-solublepolyhydric alcohol fatty acid ester in the oil and fat solvent.
 2. Theprocess for producing an oil and fat composition containing hydrophobiccomponents of licorice according to claim 1, wherein the licorice ismixed with the oil and fat solvent used together with at least oneorganic solvent selected from the group consisting of ethanol, acetone,and ethyl acetate.
 3. The process for producing the oil and fatcomposition containing hydrophobic components of licorice according toclaim 2, wherein at least one organic solvent selected from the groupconsisting of ethanol, acetone, and ethyl acetate is mixed withlicorice, and then the oil and fat solvent containing 10% by weight ormore of the fat-soluble polyhydric alcohol fatty acid ester is mixedtherewith.
 4. The process for producing the oil and fat compositioncontaining hydrophobic components of licorice according to claim 1,wherein the oil and fat solvent contains only the fat-soluble polyhydricalcohol fatty acid ester.
 5. The process for producing the oil and fatcomposition containing hydrophobic components of licorice according toclaim 1, wherein the fat-soluble polyhydric alcohol fatty acid ester isa glycerol fatty acid ester.
 6. The process for producing the oil andfat composition containing hydrophobic components of licorice accordingto claim 5, wherein the glycerol fatty acid ester is a monoglycerideand/or a diglyceride.
 7. The process for producing the oil and fatcomposition containing hydrophobic components of licorice according toclaim 5, wherein the glycerol fatty acid ester is a medium-chaintriglyceride.
 8. The process for producing the oil and fat compositioncontaining hydrophobic components of licorice according to claim 5,wherein the glycerol fatty acid ester is a polyglycerol fatty acidester.
 9. The process for producing the oil and fat compositioncontaining hydrophobic components of licorice according to claim 8,wherein the polyglycerol fatty acid ester is a polyglycerol condensedricinoleic acid ester.
 10. An oil and fat composition containinghydrophobic components of licorice produced by the process according toclaim
 6. 11. An oil and fat-containing food comprising the oil and fatcomposition containing hydrophobic components of licorice according toclaim
 10. 12. An oil and fat composition containing hydrophobiccomponents of licorice produced by the process according to claim
 7. 13.An oil and fat-containing food comprising the oil and fat compositioncontaining hydrophobic components of licorice according to claim
 12. 14.A process for producing an oil and fat composition containinghydrophobic components of licorice, comprising the steps of: providingan oil and fat solvent containing 10% or more by weight of a fat-solublepolyhydric alcohol fatty acid ester; providing licorice in a form otherthan as an extract obtained by extraction with a common organic solvent;mixing the licorice in said form with said oil and fat solventcontaining 10% or more by weight of a fat-soluble polyhydric alcoholfatty acid ester; and obtaining an oil and fat composition containinghydrophobic components of licorice by removing insolubles from themixture.
 15. The process of claim 14 further including the steps of:mixing the licorice in said form with at least one organic solventselected form the group consisting of ethanol, acetone, and ethylacetate and, then; mixing the oil and fat solvent containing 10% more byweight of the fat-soluble polyhydric alcohol fatty acid ester with thelicorice and organic solvent mixture.